Triphenylphosphine → [4-(Ethoxycarbonyl)-2-fluorobenzyl](triphenyl)phosphonium bromide

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-fluoro-4-methylbenzoate (8.586 g, 47.13 mmol) in carbon tetrachloride (70 ml) were added N-bromosuccinimide (8.388 g, 47.13 mmol) and 2,2′-azobisisobutyronitrile (309.6 mg, 1.885 mmol), and the mixture was stirred at 90° C. for 30 mins and at 100° C. for 16 hrs. The reaction mixture was cooled to 0° C., and the precipitated solid was filtered off and washed twice with hexane. The filtrate and washing solution were combined, and the mixture was washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in toluene (30 ml), and triphenylphosphine (9.891 g, 37.71 mmol) was added. The mixture was heated under reflux for 40 mins and cooled to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to give [4-(ethoxycarbonyl)-2-fluorobenzyl](triphenyl)phosphonium bromide (16.52 g, yield 67.0%) as a white solid.

Provenance & Evidence